Effective One-on-One Meetings: Leadership Practice, Reflection, and Growth

Through my experience in the MOR Leaders Program, I evolved my thinking about the purpose of effective one-on-one meetings for leaders and employees and how to get the most out of them for all involved.

I vividly remember when I first became a people manager, more than 20 years ago. Looking back, I was very much in the “managing” mindset (or more accurately, micro-managing), using one-on-ones simply to advance the work I’d assigned to my team members. Small talk for connection happened here and there, but we quickly got down to business, using their to-do list as a conversational guide. Reflection and development were not concepts on my radar in my late twenties. I prided myself on understanding the difference between important and urgent, which, hey, is not a bad thing to know.

Fast forward to my leadership style just before MOR. For years I had been soaking up the behaviors of the best leaders I’ve had the privilege of reporting to. I manage mature employees who must think like entrepreneurs to solve the daily challenges that crop up. These challenges are never the same, and invariably involve relationships and politics.

We are not looking at to-do lists. I knew that it was important for me, as their leader, to connect with them as people first and foremost, to foster reflection, and to develop their careers. But I didn’t have a lot of concrete ideas about how to go about fostering reflection. So I turned to Google, as one does. I read a lot about the best questions for effective one-on-one meetings for leaders and compiled a small bank of resources, which are shared below.

Fast forward to today, having learned so much from time with my cohort at MOR, and putting my learning into practice. My confidence in fostering reflection is much higher now. I no longer feel the need to have a scripted list of questions in front of me. I really connected with the practice of asking open-ended questions to help someone think things through on their own – without leading them to my own solution. I’m definitely always still working on that last part, but I know I will get there thanks to the practice MOR has taught us about building stackable leadership habits.

Today, I focus on having effective one-on-one meetings that will help my team think through their daily challenges, as well as help them reflect on where they want to take their career. Here is the “best of” list I gathered from my research.

Mix up your one-on-one meetings format by walking instead of sitting across a table.

Walking meetings lead conversations down literal and figurative different paths, and suit reflection and creativity. It’s also a great solution for the Zoom fatigue we all feel.  Walking together changes the dynamic; it feels less formal. Because you’re not looking at each other as much when you are walking, it can also be easier to tackle more emotionally-challenging topics.

If you are geographically separated, you can still do this by each going for a walk in your own neighborhood and connecting via phone. Voice-only is a different dynamic altogether and offers a nice change of pace.

Ask these questions after a long break, a vacation, or at review time.

I use these after winter break in January, which tends to lead to a week’s worth of the best one-on-ones.

• What were your biggest wins last year?
• What did you want to achieve but didn’t?
• What clarity have you gained over the break?
• What do you want to place more emphasis on during the next few months?

These general one-on-one questions are good anytime

• What’s on your mind?
• What’s on your plate right now, and how would you change it if you had the choice?
• What have you done recently that energized you? What took your energy away?
• What’s top of mind right now that we haven’t talked about yet?
• What’s one thing we could change about work for you that would improve your personal life?
• What’s something you wish we did better as a team?

Ask these when you want to understand how your employee feels about their work:

• How would you like to grow within this organization?
• Do you feel a sense of purpose in your job?
• What do you need from me to do your best work?
• What are we currently not doing as a team/organization that you feel we should do?
• Do you have the opportunity to do what you do best every day?

Other helpful resources focused on effective one-on-one meetings

• Harvard Business Review IdeaCast: Supercharge Your One-on-One Meetings (podcast)
• The Important Thing: The One About 1:1’s (podcast)
• Business Insider: This Is The Most Important Meeting You’ll Have. Here’s How to Make It Better.
• The Update, The Vent, and The Disaster

I hope these tips lead to effective one-on-one meetings for leaders that leave everyone involved feeling more energized, connected, purposeful, and supported.

Molly Sharp is the Director, IT Infrastructure Product Service & Strategy at Stanford University, and a MOR program alum.  Molly can be found on LinkedIn and reached at [email protected].